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What Hookers Do on Valentine's Day

Is it good to be a call girl on the most romantic night of the year? Very. Unless you’re getting engaged.

I was once a typical call girl, married to my business—wedded to my ringing phone, committed to my little black book and my regulars—which made having a boyfriend feel like infidelity.

Like other unfaithful women, I told myself the contradictions were unbearable when it was all, actually, quite delicious. My heart was constantly pulled in two directions, leading me to wonder each time I fell in love whether I could leave my career for this particular man. Deep down, many prostitutes find this idea of respectability thrilling—and a bit frightening. I loved that tension, thriving on it erotically while claiming I wanted to escape it.

I remember wistfully turning down a lucrative Valentine’s Day call in order to have dinner with a boyfriend, and feeling a flash of guilt for cheating on the business I’d been building for nearly a decade.

On any given Valentine’s Day, I took as many daytime appointments as I could because I knew I'd be stepping out in the evening. I remember wistfully turning down a lucrative call in order to have dinner with a boyfriend I'd been seeing less than a year, and feeling a flash of guilt for cheating on the business I'd been building for nearly a decade.

Is Valentine’s Day a good day for the sex industry? That all depends. If you’re a call girl, it's often a great night to be
without a valentine—coworkers are being romanced by boyfriends, which means demand for professional companionship might outstrip supply. But it's hard to predict. For those clients seeking a Valentine’s experience, complete with candy, rose petals and Champagne, you need a girl who's a lot more professional than she appears to be. Business varies from year to year, so ending a romance before the big holiday just for the purpose of being on call would be foolhardy, and most hookers aren't that calculating. Because romance serves as a much-needed vacation from the marketplace, the 14th —for a madam—is a potential headache, a night when you sometimes run short of girls.

It's a day that sums up all that's “wrong and romantic” about being a call girl. Qualities that spell success in the oldest profession—symmetrical features, a sweet smile, an open personality and a fondness for male company—also attract boyfriends. A recipe for conflict.

I tried not to get involved with anyone so I could focus on business, but I was a boyfriend-magnet. My biggest problem wasn't the stigma associated with my work, it was my tendency to fall in love. A few years later, I found myself “cheating” again, with someone new.

R and I were introduced by a married couple who enjoyed playing Cupid for their pet bachelor, a junior I-banker. A guy from the wrong side of the tracks who had put himself through business school, he was still paying off his student loans. I've always been partial to men who have to make it on their own. After our fourth date, I decided not to hide my work from him.

When I pointed out that I'd been in bed with more women than he had—"and I'm not even into girls!"—he laughed. He admired me for being a self-made woman, and wanted me to meet his mother, though we stopped short of telling his family about my scarlet career.

I thought I was rather edgy, a former teen runaway thumbing her nose at society, but as February 14 rolled around I couldn’t help falling for the most saccharine of romantic conventions with R. I decided to serve a heart-shaped meatloaf. After dinner, we sat on my couch, pleasantly tipsy on Cabernet, and R produced a book written by Richard Nixon. “The title made me think of you,” he said. When I got to the title page, I saw that the book had been carefully defaced—there was a square hole where the words “America's Challenge” should have been, and just below the title, “Seize the Moment,” was a two-carat diamond ring, glittering above the words “One Superpower World.”

I was an unrepentant prostitute experiencing the ultimate bourgeois fantasy: getting engaged on Valentine's Day. Showing my ring to customers and coworkers, I felt like a scrappy, unknown athlete who’d just landed an Olympic gold medal. I had to remove the ring during sex to avoid damaging my customers' tender body parts, but I was beaming with pride—I had hacked the system. The system that says you can’t tell a normal middle-class guy what you do for a living and be with him in any serious way.

People assume that a call girl lies to her boyfriend about her work, but it's not that simple. Sometimes call girls lie to each other about what we've told our boyfriends. This can make things…complicated. For instance, my best friend Jill didn't want R to know she was a call girl. I didn't want her lecturing me about what she thought I was doing wrong, so I lied to her and said he didn’t know
I was a call girl. After working all week, sometimes together, Jill and I would go on double dates with our respectable boyfriends—who must never, ever find out what we did for a living. I had an obligation to protect her, so I told R that Jill would be “shocked if she knew." I was lying to my best friend and my fiancé, but as tangled as it got, I felt it was for a good cause. And somehow, because we all loved going out for sushi together, the intrigue and confusion were worth it.

But once I started wearing a ring—
his ring—R grew jealous of my customers. He was trying to be open-minded, but he would get upset if I couldn't see him on a weeknight, and I loved him too much to tell him to get stuffed. He was putting pressure on me to renounce my career, but it was a difficult choice. I was proud of the business I had built. Having worked so hard to get where he was, R understood my dilemma—at first. But when we moved in together, he became less sympathetic, more openly possessive, and I grew nervous.

That's when I met Julian. I knew right away that Julian wasn't going to be threatened by my unusual career—because he was a male escort. As we exchanged numbers, I found myself fantasizing about a partnership. I'd heard about some of those happily married porn-star couples. Maybe they had it all figured out. Could Julian be the answer?

He entertained me with stories about rich married ladies and said that sex with me—or rather, with him—would be "a professional courtesy."

Wait.

A ... professional what?

The idea of sex with a guy who normally gets paid for it began to unnerve me. "Professional courtesy" made our hypothetical encounter sound too much like a transaction. Would he think of me as a nonpaying customer? But I had every right to think of
him that way! Two sex-industry egos colliding wasn't the answer at all.

R's reaction to my career had produced a romantic sizzle that was missing from my flirtation with Julian. I began to concentrate on my writing, but left my call-girl options open. I wanted to abstain from escorting—up to a point—and R was happy to support me. But when I wasn’t seeing customers I felt trapped. Flashing my bourgeois trophy around made me feel naughty and subversive, but settling down for real felt like defeat.

I started worrying about the logistics of our lives together and wondering if I could fit into R's world—the corporate wives were terrifying! What if word got around the office that R's wife had been a hooker since her teens? What would that do to his career? R thought having a baby would protect us: "Nobody wants to be seen bad-mouthing the mother of a guy's child." In other words, he wanted me to be the CEO of his DNA. I wasn't convinced.

Children and work began to divide us. R and I spent months in couples' therapy trying to connect the dots. There were things we never had the courage to talk about, but when we separated, it was a civilized, surprisingly tender parting of the ways.

As Valentines go, a diamond engagement ring is the ultimate trophy, and I still have the ring R gave me, but my trophy has become a souvenir of something more lasting—a lesson about the realities of love trumping the symbolism of a holiday.